Enantioselective protonation is a versatile approach to the construction of tertiary α-stereocenters, which are common structural motifs in various natural products and biologically relevant compounds. Herein we report a mild access to these chiral centers using cooperative gold(I) catalysis. From cyclic ketone enol carbonates, this asymmetric catalysis provides highly enantioselective access to cyclic ketones featuring an α tertiary chiral center, including challenging 2-methylsuberone. In combination with the gold-catalyzed formation of cyclopentadienyl carbonates in a one-pot, two-step process, this chemistry enables expedient access to synthetically versatile α′-chiral cyclopentenones with excellent enantiomeric excesses from easily accessible enynyl carbonate substrates. 
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                            Alkyne Trifunctionalization via Divergent Gold Catalysis: Combining π-Acid Activation, Vinyl–Gold Addition, and Redox Catalysis
                        
                    - Award ID(s):
- 1665122
- PAR ID:
- 10295413
- Date Published:
- Journal Name:
- Journal of the American Chemical Society
- Volume:
- 143
- Issue:
- 10
- ISSN:
- 0002-7863
- Page Range / eLocation ID:
- 4074 to 4082
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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